Deals don’t fail on spreadsheets—they fail in time. We sit down with Jack to unpack how a former capital placement pro in New York became an owner-operator in Philadelphia by pairing finance discipline with architectural execution. From multifamily and mixed use to a surprising run of gas station c-stores, he shares what it takes to make lenders compete, why term sheets are won with clarity, and how vertically integrated design, permitting, and development cuts friction and cost.

We get honest about negative leverage—when it’s a calculated bridge to value and when it just steals your sleep. Jack breaks down the most common investor mistake he sees: moving the goalposts to “make it work.” His fix is simple and hard—standardize your underwriting, define your return targets before you chase a deal, and compress timelines with prepared scopes, zoning paths, and lender-ready packages. We also demystify rate chatter: the Fed funds target isn’t the 10-year Treasury, and yields can rise after a cut. Materials and labor keep supply tight, which props up well-bought assets while punishing loose underwriting.

You’ll hear how Jack raised capital from friends, former colleagues, and lean family offices by offering straight terms and a team that can draw, permit, and build. We dive into leverage selection using exit multiple, not ego, and why sharing recourse only works with partners who prize the product and the neighborhood as much as the return. If you care about building real, lasting value—through mixed-use activation, clean design, and crisp execution—this conversation gives you the playbook.

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VCap Real Estate Podcast